Short Term Rental Secrets Podcast

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The Short Term Rental Secrets Podcast is dedicated to providing actionable content to help new and seasoned real estate investors launch, automate and scale their Airbnb business and fast track their journey to financial freedom. You can enjoy the podcast and other free resources at www.STRsecrets.com

  1. Every Objection That's Costing You Clients — Handled Live on Stage at Our Acquisitions Event

    1D AGO

    Every Objection That's Costing You Clients — Handled Live on Stage at Our Acquisitions Event

    If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply If you want to join our weekly free training: https://www.facebook.com/groups/STRentalsecrets This one is different. At our last STR acquisitions event at the Freedom Factory in Beverly, MA, we did something we'd never done before. We filled a hat with real homeowner objections — things operators hear every day — and had four coaches handle them live on stage in front of 50 operators. No prep. No script. No safety net. Coaches Mike Reilly, Dave, Darryl, and E took turns handling objections like "your fees are too high," "you're not local," "I don't want to be locked in," and "I want to take advantage of the STR tax loophole." Each coach handled them differently — because that's the point. There is no single right answer. There's the answer that fits your voice. This is an hour of live, unfiltered STR sales training recorded in the room. If you're growing a property management or cohosting business, this episode will change how you handle objections. Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

    1h 3m
  2. 5 Years. 180 Properties. 36 People. Aidan Groll on Building a Real STR Management Company

    5D AGO

    5 Years. 180 Properties. 36 People. Aidan Groll on Building a Real STR Management Company

    If you want to increase your revenue, automate your day to day operations and spend more time with your kids, talk to us: http://strsecrets.com/apply If you want us to review your listing, org chart, pricing or anything related to STR business, join here: ➡ https://www.facebook.com/groups/STRentalsecrets Most STR companies obsess over guest reviews. Blue Gems obsesses over owner profitability. And they grew to 180 properties under management doing it. In this episode, recorded live at the Freedom Factory in Beverly, MA, E and Chris sits down with Aidan Groll — co-founder of Blue Gems Management, one of Florida's fastest-growing STR companies. Aidan and his partner JB manage 180+ properties across Orlando and Clearwater Beach with a 36-person team — and grew almost entirely through organic relationships, not paid ads. In this episode Aidan breaks down: - How he went from a corporate accounting job to buying his first duplex in March 2020 - How a 400 sq ft backyard ADU made $50K in its first year and convinced him to go all in on STRs - Why Blue Gems puts owners 70% over guests — and how they pitch that to new clients - Their full org chart at 180 units: 14 in maintenance, 7 in guest experience, 3 in sales and more - Why they do ALL maintenance in-house — and why speed was the deciding factor - How they automated 70% of guest communication with AI in the last year - Their 7-day contract-to-live-listing goal and how they hit it consistently - How they choose markets based on regulatory stability — not just cash flow - Why they shut down their podcast and social media for 2+ years to focus on growth - Their plan to reach 350-400 units through acquisitions of smaller operators - The Valley of Disappointment — and why most people quit right before it gets good - Aidan's #1 secret to STR success: patience This is a masterclass in building a real, scalable STR management business. --- About Aidan Groll: Aidan Groll is the co-founder of Blue Gems Management, an Orlando-based vacation rental management company that has grown to oversee 180+ properties across Florida. Originally a real estate investor with a background in corporate accounting, Aidan and his business partner JB pivoted to short-term rentals in late 2021 — building their own management infrastructure before opening to third-party clients in early 2023. Since then, Blue Gems has scaled to a 36-person team with full in-house maintenance operations, serving property owners across Orlando and Clearwater Beach. Time Stamps: 0:00 - intro 0:54 - Introducing Aidan Groll and Blue Gems Management 1:28 - What Blue Gems Does Differently (Owner-First Philosophy) 4:14 - The Real Cost of Building This Business 5:08 - Aidan's Origin Story: From Accounting Job to House Hacking in 2020 7:54 - The $50K ADU That Changed Everything 9:10 - Scaling to 180 Properties: How Blue Gems Grew Without Paid Ads 10:46 - The Contrarian Take: Why They Don't Chase 5-Star Reviews 13:46 - How to Pitch the Owner-First Model to New Clients 18:26 - Inside the Org Chart: 36 People, 180 Properties 20:08 - Why They Do All Maintenance In-House 25:38 - How AI Automated 70% of Guest Communication 29:54 - From Signed Contract to Live Listing in 7 Days 31:18 - How to Choose Markets Based on Regulatory Stability 36:49 - Why Aidan Is Selling His Portfolio to Bet on the Management Company 40:41 - The Real Cost of Building This Business 43:59 - The Future: 350+ Units and Acquiring Smaller Operators 47:15 - Aidan's #1 Secret to STR Success Connect with Aidan: Instagram: https://www.instagram.com/aidangroll/ LinkedIn: https://www.linkedin.com/in/aidan-groll Email: aidan@bluegems.group 📲 Connect with STR Secrets: Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets STR Secrets Podcast: https://strsecrets.com/podcast

    49 min
  3. We Pulled Up 2 Real Airbnb Listings and Told Them Everything That's Wrong | STR Portfolio Clinic #1

    MAR 26

    We Pulled Up 2 Real Airbnb Listings and Told Them Everything That's Wrong | STR Portfolio Clinic #1

    Resources mentioned in this episode are available at: strsecrets.com/clinic If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply If you want to join these live trainings: https://www.facebook.com/groups/STRentalsecrets This is the first episode of the STR Portfolio Clinic. A brand new series where me and Mike Sjogren pull up real STR listings on screen and diagnose what's working and what's not. Live. In front of everyone. No filter. This episode is all about listings. We reviewed two real Airbnb properties from operators who volunteered to put their listings on the hot seat. First up is a brand new beach cottage in Oak Island, North Carolina. Second row from the ocean. Clean listing. But nobody's clicking on it. We broke down why and gave the owner a full game plan on the spot. Then we pulled up a riverfront property in Murphy, North Carolina. Fly fishing right off the deck. Beautiful area. Went an entire summer with zero bookings. It took about 10 seconds to see what was wrong. We also break down the ALE framework which stands for amenities, location, and experiences. This is the framework behind how we build listings across 30+ properties that generated over $5M in bookings last year. If your listing has been sitting or your bookings have slowed down, this episode will show you exactly what to fix and in what order. Want your listing or business reviewed on a future episode? Drop CLINIC in our DMs TIMESTAMPS: 0:00 - What is the Portfolio Clinic 0:55 - The ALE Framework: Amenities, Location, Experiences 4:17 - Listing Review #1: Beach Cottage in Oak Island, NC 5:09 - Photo feedback: It's clean but it's too white 6:31 - How to use AI for sunset and lifestyle shots 7:15 - Staging amenities: Reilly's beach property example 8:41 - Who's your avatar and why it changes your photos 9:12 - Sjogren: The wizard room hero image strategy 10:33 - Using ChatGPT to create twilight shots 11:38 - Interior updates vs working with what you have 12:47 - Getting five star reviews on a new listing 13:52 - The combined listing strategy for side by side properties 16:58 - Aerial shot hack to show both properties 17:48 - Listing Review #2: Riverfront A-Frame in Murphy, NC 18:16 - Sjogren's first reaction: "I don't love this first photo" 19:04 - Andy's story: Zero bookings since launch 19:56 - Why you need to relaunch dead listings 20:35 - Phone photos are killing your listing 21:24 - What lifestyle photos this property actually needs 22:47 - Comp analysis: What top properties in Murphy look like 25:02 - Brutal feedback: The photos make it look dark and dated 26:35 - Staging the deck and outdoor space 28:41 - The game plan: Photos, relaunch, pricing, reviews 29:42 - The Airbnb new listing push and why Andy missed it 30:09 - Small changes that pay for themselves in one night 30:47 - Insurance and liability for offering amenities 33:23 - Bonus: Quick review of Christie's listing 35:40 - What's coming next and the Freedom Factory event

    37 min
  4. Why You Keep Self-Sabotaging Even When You Know Exactly What to Do

    MAR 23

    Why You Keep Self-Sabotaging Even When You Know Exactly What to Do

    YOUTUBE DESCRIPTION Most people end Q1 the same way they started it. Behind on goals. Ahead on excuses. In this solo episode, E breaks down why that happens — and what to actually do about it before Q2 starts. This isn't a motivational pep talk. It's a direct, honest look at the real reason you keep self-sabotaging — even when you know exactly what you need to do. In this episode, E covers: - Why the brain doesn't perceive time as time — and what that means for how you're living - Tony Robbins' 3 S's framework: State → Story → Systems (and why you're skipping the first two) - The 5 core wounds that create self-sabotage: rejection, abandonment, humiliation, betrayal, and injustice - The difference between being self-centered vs. self-aware — and why it changes everything - The belief thermostat: why you always reduce yourself back to what you think you're worth - 3 questions to ask yourself right now as you close out Q1 - The one question E asks himself that "terrifies the shit out of him" — and keeps him moving If the year hasn't gone the way you planned — this episode is the reset you need. 📲 Connect with STR Secrets: Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets Apply to work with us: https://strsecrets.com/apply STR Secrets Podcast: https://strsecrets.com/podcast Timestamps: 0:00 - Intro 2:09 - Q1 Check-In: Are You Still Holding Your Standards? 3:57 - Why Time Feels Like It's Running Away (The Science of Memory Markers) 6:13 - Stop Just Learning — Start Experimenting 7:13 - Tony Robbins' 3 S's: State, Story, and Systems 9:23 - Why Mindset Work Alone Keeps Failing You 9:47 - The 5 Core Wounds Behind Every Self-Sabotage Pattern 11:23 - How Your Brain's 3 Layers Are Keeping You Stuck 13:38 - Self-Centered vs. Self-Aware: The Shift That Changes Everything 15:37 - The Belief Thermostat: Why You Keep Reducing Yourself 17:05 - Your Honest Q1 Review: Facts Only, No Stories 18:38 - 3 Questions to Ask Yourself Before Q2 Starts 20:33 - Nobody Is Coming to Save You 22:56 - "Is This the Final Version of You?"

    24 min
  5. Your Listings Are Dying on Airbnb — Here's Exactly How to Fix It with Maryann Wahhab

    MAR 19

    Your Listings Are Dying on Airbnb — Here's Exactly How to Fix It with Maryann Wahhab

    If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply Check out our free 6 step course: https://level.strsecrets.com/pc-book If you want to join these live trainings: https://www.facebook.com/groups/STRentalsecrets If your listings aren't getting booked right now — don't panic and drop your prices. In this week's Thursday training, Mike Reilly sits down with Maryann Wahhab, revenue management expert and STR operator across 6 states, to break down exactly what's working right now to get booked at the rates you want. Maryann went from college basketball coach to full-time STR revenue manager — and now helps operators stop leaving money on the table in soft markets. In this episode, Mike and Maryann cover: - Why your slow bookings are probably a listing problem — not a pricing problem - The booking window zones every operator needs to understand (and how to price each one) - How Mike went 30% up year over year on Vrbo with one simple OTA trick - The "booking velocity" metric Maryann tracks at 7, 15, and 30-day marks - How a listing went from page 6 to page 2 on Airbnb in one week - Why virtual stays are a game changer for dead listings - The full listing re-optimization playbook for properties with no bookings in 30+ days - How to use Airbnb's rule sets and length-of-stay discounts to capture more revenue in slow season This is the training your listings need right now. --- 🎙️ About Maryann Wahhab: Maryann is a revenue management expert and STR operator managing properties across 6 states. A former Division I basketball coach, she left the game in 2023 to manage properties full-time — and now helps STR operators maximize revenue in any market condition. --- Timecodes: 0:00 - Why Your Listings Aren't Getting Booked Right Now 2:30 - Meet Maryann Wahhab: From Basketball Coach to STR Expert 6:00 - How to Read Your Market Before You Touch Your Prices 10:00 - Booking Window Zones Explained (And How to Price Each One) 15:30 - Booking Velocity: The Metric That Tells You When to Act 20:00 - How to Play the Airbnb and Vrbo Algorithm Game 25:30 - The OTA Trick That Got Mike 30% Up Year Over Year on Vrbo 30:00 - Virtual Stays and How to Reinvigorate a Dead Listing 36:00 - The Full Re-Optimization Playbook for Struggling Listings 41:30 - Length-of-Stay Discounts and Airbnb Rule Sets in Slow Season 46:00 - How to Differentiate Your Listing So You're Never in a Price War

    38 min
  6. The 'Help First' Sales Mindset That Grew Them From 12 to 120 Properties with Sean Bakhtiari

    MAR 16

    The 'Help First' Sales Mindset That Grew Them From 12 to 120 Properties with Sean Bakhtiari

    Connect with Sean: Instagram: https://www.instagram.com/sean_bakhtiari/ Check out Seacoast 2 Summit: https://www.seacoast2summit.com Check out our free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets What happens when a corporate finance guy from Boston decides he's done working for someone else — and bets on short-term rentals? Sean Bakhtiari is the co-founder of Seacoast 2 Summit Vacation Rentals and The Bakhtiari Group, a top-performing real estate sales team across Massachusetts, New Hampshire, and Maine. As an active STR investor, his work sits at the intersection of real estate, hospitality, and investment strategy throughout New England. After 9 years in Boston's financial district, Sean bought his first STR. Then a second. Then started building a management company. At 12 properties, he hit a wall. He was good at business development and client relationships. But systems, operations, and scale? Not his strengths. That's when a serendipitous call from Chris changed everything. Today, Sean and Chris co-run Seacoast to Summit Vacation Rentals — managing 120+ properties across the New Hampshire seacoast, lakes and mountains region, and North Shore of Massachusetts. Almost entirely on referrals, with virtually no paid marketing. In this episode, Sean and Chris pull back the curtain on: - How they identified each other as the right partner (and what 3 things you need to align on before you sign anything) - Sean's "help first, never sell" philosophy — and why it's responsible for most of their growth - Why they've said no to 10+ deals in the last 3 months (and why that's the right call) - The two fears they stay up at night thinking about as they scale - How to delegate without feeling like you're losing control - What it takes to keep your team culture intact as you grow - Why boutique hotels might be the next frontier for this business This is a rare episode — a founder bringing on his business partner and pulling off the veil on how a real, values-driven STR company actually works at scale. --- Timestamps: 0:00 - Introducing Sean Bakhtiari: Chris's Business Partner 2:45 - How Sean Went From Corporate Finance to STR Management 6:30 - Building Seacoast to Summit: From 12 to 120 Properties 10:15 - How Sean and Chris Found Each Other (The Serendipitous Call) 15:00 - The 3 Things You Must Align On Before Partnering 18:30 - The "Help First" Sales Mindset That Built the Business 23:00 - Why They Said No to 10 Deals in 3 Months 27:00 - The Two Fears They Have About Growing Too Fast 32:30 - How to Delegate Without Losing Control 37:00 - Keeping Team Culture Intact at Scale 42:00 - What the Future Looks Like: Boutique Hotels and Brand Building 46:00 - Sean's #1 Secret to STR Success

    43 min
  7. From Rock Bottom to 18 Properties: How Jeremiah Quit His Job and Built a Real Business

    MAR 12

    From Rock Bottom to 18 Properties: How Jeremiah Quit His Job and Built a Real Business

    Connect with Jeremiah: Instagram: @jeremiahkwatson Business: www.affluentvacays.com Check out our free 6 step course: https://level.strsecrets.com/pc-book STR Secrets FB group https://www.facebook.com/groups/STRentalsecrets He did everything people told him to do. Got clean. Went to college. Got a good job. Made good money. And he was still unhappy. In this episode, we talk with Jeremiah Watson. Jeremiah just quit his corporate job. He now runs an 18-property cohosting business in Los Angeles. He is the 73rd person to leave their job through STR Secrets. Here's what you'll learn: → How Jeremiah went from addiction and jail to building a real business → Why he lost $50K his first year — and what he changed → How he got his first cohosting deal with one cold call → The small team that runs his business today → His goal: 66 properties by the end of 2026 This is what actually doing the work looks like. Timestamps: 00:00 - Who Is Jeremiah Watson? 03:12 - From Addiction and Jail to Turning His Life Around 08:11 - Why He Chased the Corporate Dream 11:36 - He Tried STRs and Lost $50K in Year One 13:16 - How He Found Cohosting and Got His First Deal 16:36 - How He Grew From 1 to 18 Properties 19:11 - His Team and How the Business Runs Today 21:27 - His Big Goal: 66 Properties by End of 2026 22:45 - What to Do If You Have a Job and No Time 27:06 - How to Balance Drive With Gratitude 31:57 - Why This Business Is About More Than Money

    38 min
  8. Ep - 284 Why Most STR Operators Fail at Hiring (Leadership Masterclass) with Alex Hall

    MAR 9

    Ep - 284 Why Most STR Operators Fail at Hiring (Leadership Masterclass) with Alex Hall

    Scaling a short-term rental company isn’t just about getting more properties. It’s about building the team that can support the growth. In this episode, Chris and E sit down with Alex Hall — talent advisor and leadership strategist — to break down the real challenges STR operators face when building teams. From job clarity and org structure to burnout, hiring, and leadership development, Alex shares the frameworks that help operators scale from a handful of listings to a real company. If you're trying to grow beyond the stage where you do everything yourself, this episode is a masterclass in leadership and people management. Inside this episode: • Why most STR companies don’t actually know who reports to who • The biggest hiring mistake operators make while scaling • How to structure a team from 10 to 100+ listings • Why burnout happens during fast growth • The leadership habits that retain great talent • When to introduce equity or long-term incentives If you want a real business — not just a portfolio of properties — it starts with leadership. Guest Bio: Alex Hall is the founder of Valinor Talent Solutions, where he serves as a fractional HR executive helping growing companies build strong people strategies, leadership development, and scalable teams. With over a decade of experience in talent and organizational development, he partners with businesses to create high-performing workplaces. Alex works with short-term rentals to develop their talent strategy so they can focus on delivering exceptional guest experiences through thoughtful design, strong systems, and hospitality-driven service. Guest Contacts: alex@valinortalent.com www.valinortalent.com Get FREE Access to our 6 STEP course: https://www.strsecrets.com/podcast Timestamps: 00:00 – Why Most Teams Don’t Know Their Role 02:00 – Success, Identity, and Leadership Growth 04:30 – Introducing Alex Hall: Talent Advisor for STR Operators 07:25 – When STR Businesses Actually Need HR Support 09:20 – The 3 Levels of Team Structure as You Scale 12:40 – The Most Common Hiring Problems in STR Companies 14:00 – Why Job Clarity and Accountability Are Missing 17:10 – The 33% Rule: When Leaders Outgrow Their Team 20:05 – Burnout Signals Every Operator Should Watch 23:20 – Building Org Structures for 10–100 Listings 26:00 – Why Systems Matter More Than Org Charts 27:00 – How Great Leaders Reward and Motivate Teams 30:00 – Equity vs Performance Bonuses for Key Employees 33:00 – The 3 Rules of Leadership: Clear, Kind, Respectful 36:10 – Leadership Lessons for First-Time Founders 39:50 – AI’s Role in Future STR Operations 42:40 – Final Advice for Building a Great STR Team

    43 min
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About

The Short Term Rental Secrets Podcast is dedicated to providing actionable content to help new and seasoned real estate investors launch, automate and scale their Airbnb business and fast track their journey to financial freedom. You can enjoy the podcast and other free resources at www.STRsecrets.com

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